Tag: M.W=100-200

Synthetic Route of 934-32-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 934-32-7 name is 1H-Benzo[d]imidazol-2-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: In a typical experiment, different aromatic aldehyde (1 mmol),1,3-cyclic diketon (1 mmol), 2-amino-benzimidazole (1 mmol) andcatalyst (0.019 g) in solvent free condition were taken in a 25 mLround bottomed flask. The flask was stirred at 100C for an appro-priate time. The reaction mixture was cooled, eluted with hotethanol (5 mL), centrifuged and filtrated to collect the formed pre-cipitate. The crude product was recrystallized from ethanol to yieldpure benzimidazoloquinazolinone derivatives.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Amoozadeh, Ali; Rahmani, Salman; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 96 – 107;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 70631-95-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 70631-95-7 as follows.

Compound 14.3. 5-Iodo-4-methyl-lH-imidazole-2-carbonitrile. Into a 25-mL round bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 4-methyl- lH-imidazole-2-carbonitrile (compound 14.2, 350 mg, 3.27 mmol) and aqueous sodium hydroxide (2 M, 5 mL) and stirred for 15 min at room temperature. This was followed by the drop-wise addition of a solution of iodine (1.25 g, 4.92 mmol) in dichloromethane (5 mL). The resulting mixture was stirred for 24 h at room temperature, then diluted with water/ice (10 mL). The aqueous layer was washed with DCM (10 mL), and then the aqueous layer was acidified to pH 5-6 with acetic acid. The aqueous phase was extracted with EtOAc (5 x 50 mL) and the combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure to yield 500 mg (66%) of the title compound as a brown solid.

According to the analysis of related databases, 70631-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 29043-48-9

A solution of 75 mg (0.10 mmol) of (2S) -2- {[(iraws-4- {[(ieri-butoxycarbonyl) – amino] methyl}cyclohexyl) carbonyl] amino} -3- (4 ‘- {[1 – (ieri-butoxycarbonyl) -piperidin-4-yl] – carbamoyl} -2’-methyl-biphenyl-4-yl) propanoic acid and 31 mg (0:21 mmol) of 2-methyl-l / ibenzimidazol-5-aminewas dissolved in 1 ml of dichloromethane containing 0.05 ml (0:31 mmol) of N, N-diisopropylamineand 81 mg (0:16 mmol) of (l / i-benzotriazol-l-yloxy) (tripyrrolidin-lyl) phosphoniumhexafluorophosphate was added and stirred for 16 h at RT. The reaction solution was separatedby preparative HPLC (eluent: acetonitrile / water gradient, 0.01% to trifluoroacetic acid). Theproduct-containing fractions were combined and concentrated on a rotary evaporator. There were23 mg (26% d. Th.) Of the title compound.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERT ALAN; SCHMIDT, MARTINA VICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (489 pag.)TW2016/5810; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 37052-78-1, name is 5-Methoxy-1H-benzo[d]imidazole-2-thiol, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2OS

Reference Example 12 Production of 4-(5-methoxybenzimidazole-2-ylthio)butanoate ester hydrogen bromide salt 6.48 g (33.2 mmol) of 4-bromobutanoate ethyl ester were added to 10 ml of an ethanol solution containing 5.0 g (27.7 mmol) of 5-methoxybenzimidazole-2-thiol followed by stirring for 1 hour at 80 C. and adding 90 ml of ethyl acetate. The reaction solution was returned to room temperature and the formed crystals were filtered out followed by drying to obtain 9.34 g of the target compound (yield: 90%). 1H-NMR (270 MHz, CDCl3) (ppm): 7.65 (d, 1H, J=8.91 Hz), 7.24 (s, 1H), 7.00 (dd, 1H, J=2.43, 8.91 Hz), 4.21 (q, 2H, J=7.29 Hz), 3.83 (s, 3H), 3.74 (m, 2H), 2.61 (m, 2H), 2.10 (m, 2H), 1.30 (t, 3H, J=7.29 Hz)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; TEIJIN LIMITED; US2005/267148; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 50995-95-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 50995-95-4 as follows.

[0675] A solution of 2-propylimidazole (76 mg, 0.69 mmol) in 1 mL DME was added to a mixture NaH (32 mg, 0.81 mol, 60% dispersion in mineral oil) at 0 C under argon. After 20 min, a solution of the product of Example 157 Step 3 (250 mg, 0.62 mol) in 2 mL DME was added at 0 C. The reaction was warmed to 25 C. After 1.5 h, the reaction was filtered through a pad of Celite (1″), and washed with EtOAc (20 mL). The filtrate was concentrated to give a pale brown oil in 0.21 g (80%).

According to the analysis of related databases, 50995-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, A new synthetic method of this compound is introduced below., Quality Control of 2-(1H-Imidazol-1-yl)ethanol

Add sodium hydride (0.79 g; 1.1 equiv; 19.75 mmoles) slowly to a 0 C. solution of 1H-imidazole-1-ethanol (2.01 g; 1.0 equiv; 17.93 mmoles) in tetrahydrofuran (90 mL). Stir for 1 hour, then add acetic acid, bromo-, 1,1-dimethylethyl ester (4.03 mL; 1.49 equiv; 26.76 mmoles) dropwise at 0 C. Warm the solution to ambient temperature and stir for 3 hours, then add 250 mL saturated aqueous sodium bicarbonate solution. Extract the mixture with dichloromethane (3*150 mL). Wash the combined organic extracts with brine (100 mL), dry over sodium sulfate, filter, and concentrate to afford the crude product. Purify this residue by column chromatography (0 to 20% methanol in dichloromethane) to afford tert-butyl 2-(2-imidazol-1-ylethoxy)acetate (0.85 g; 21%) as a viscous yellow-brown oil: MS (m/z): 227(M+1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Eli Lilly and Company; Beauchamp, Thomas James; Dao, Yen; Jones, Spencer Brian; Norman, Bryan Hurst; Pfeifer, Lance Allen; US2014/200231; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, This compound has unique chemical properties. The synthetic route is as follows., name: (1H-Imidazol-1-yl)(phenyl)methanone

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10364-94-0.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of (1-Methyl-1H-imidazol-4-yl)methanol

190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 % yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).

The synthetic route of 17289-25-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 19225-92-4,Some common heterocyclic compound, 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, molecular formula is C5H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40 C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (11 mg, 29%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6514971; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53710-78-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under ice-cooling, 1-(3-chloropropyl)-1H-imidazole (1.90 g, 13.14 mmol), cesium carbonate (4.28 g, 13.14 mmol) and a catalytic amount of potassium iodide were dissolved in DMF (30 mL).2-Fluoro-4-nitroaniline (1.38 g, 8.84 mmol) was added in one portion and the reaction was heated to reflux for 36 h.After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solvent was evaporated under reduced pressure. The residue was added to water (50 mL) and extracted with dichloromethane (20 mL ¡Á 2).The organic phase was washed with saturated brine (20 mL¡Á2), the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography (dichloromethane/methanol (V/V)=15/1).A yellow oil (2.85 g, 82%) was obtained.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem